三光气“一锅法”合成异氰酸酯丙烯酸乙酯

以乙醇胺盐酸盐(2)为原料,与丙烯酰氯进行酯化反应制得丙烯酸氨基乙酯盐酸盐(3),中间体无需分离,在三乙胺作用下,经三光气羰基化反应得到目标产物异氰酸酯丙烯酸乙酯(1,AOI)。考察了反应温度、反应时间、反应物配比对反应的影响,得出的优化反应条件为:n(乙醇胺盐酸盐)∶n(丙烯酰氯)∶n(三乙胺)∶n(三光气)=1∶1.2∶3.0∶0.45,第一步反应温度为50℃,反应时间为5 h;第二步反应温度为80℃,反应时间为3 h,在该条件下反应总收率为72.5%,GC纯度99.5%。

One-pot Synthesis of 2-Isocyanatoethyl Acrylate from Triphosgene

An efficient synthesis of 2-isocyanatoethyl acrylate（1,AOI）from 2-aminoethanol hydrochloride（2）was developed. Reaction of 2-aminoethanol hydrochloride with acryloyl chloride afforded 2-aminoethyl acrylate hydrochloride（3）,which was further reacted with triphosgene without separation to produce the target product 2-isocyanatoethyl acrylate（1）. Various factors including reaction temperature,reaction time and molar ratio of raw materials were studied. The optimized reaction conditions were as follows ： n（ 2-aminoethanol hydrochloride） ∶n（acryloyl chloride）∶n（triethylamine）∶n（triphosgene）=1∶1.2∶3.0∶0.45,the first step reaction temperature was 50℃and reaction time was 5 h,the second step reaction temperature was 80℃ and reaction time was 3 h. Under the optimal conditions,the toverall yield of 1 was 72.5% with 99.5% purity.